Butylated hydroxyanisole

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"E320" redirects here. For the British high speed train known as Eurostar e320, see British Rail Class 374. For the Italian locomotive, see FS Class E.320. For E320 cars, see Mercedes-Benz 320. For the notebook computer E320, see ThinkPad E series.
Butylated hydroxyanisole
2-tert-Butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole 2D.svg
Names
Preferred IUPAC name
2-tert-Butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol (mixture)
Other names
  • 2-tert-Butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole (mixture)
  • BOA
  • BHA
  • tert-Butyl-4-hydroxyanisole
  • (1,1-Dimethylethyl)-4-methoxyphenol
  • tert-Butyl-4-methoxyphenol
  • Antioxyne B[1]
Identifiers
  • 25013-16-5 checkY
  • 121-00-6 (2-tert) checkY
  • 88-32-4 (3-tert) checkY
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.042.315 Edit this at Wikidata
E number E320 (antioxidants, ...)
UNII
  • InChI=1S/2C11H16O2/c1-11(2,3)9-7-8(13-4)5-6-10(9)12;1-11(2,3)9-7-8(12)5-6-10(9)13-4/h2*5-7,12H,1-4H3 checkY
    Key: CZBZUDVBLSSABA-UHFFFAOYSA-N checkY
  • InChI=1/2C11H16O2/c1-11(2,3)9-7-8(13-4)5-6-10(9)12;1-11(2,3)9-7-8(12)5-6-10(9)13-4/h2*5-7,12H,1-4H3
    Key: CZBZUDVBLSSABA-UHFFFAOYAZ
  • O(c1ccc(O)cc1C(C)(C)C)C.O(c1ccc(O)c(c1)C(C)(C)C)C
Properties
C11H16O2
Molar mass 180.247 g/mol
Appearance Waxy solid
Density 1.0587 g/cm3 at 20 °C
Melting point 48 to 55 °C (118 to 131 °F; 321 to 328 K)
Boiling point 264 to 270 °C (507 to 518 °F; 537 to 543 K)
Insoluble in water
Solubility Freely soluble in ethanol, methanol, propylene glycol; soluble in fats and oils
1.5303 at 589.3 nm[2]
Related compounds
Related compounds
 Butylated hydroxytoluene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N  (what is checkY☒N ?)
Infobox references

Butylated hydroxyanisole (BHA) is an antioxidant consisting of a mixture of two isomeric organic compounds, 2-tert-butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole. It is prepared from 4-methoxyphenol and isobutylene. It is a waxy solid used as a food additive with the E number E320. The primary use for BHA is as an antioxidant and preservative in food, food packaging, animal feed, cosmetics, rubber, and petroleum products.[3] BHA also is commonly used in medicines, such as cholecalciferol (Vitamin D3), isotretinoin, lovastatin, and simvastatin, among others.

Antioxidant properties[]

Since 1947, BHA has been added to edible fats and fat-containing foods for its antioxidant properties as it prevents rancidification of food which creates objectionable odors.[4] Like butylated hydroxytoluene (BHT), the conjugated aromatic ring of BHA is able to stabilize free radicals, sequestering them. By acting as free radical scavengers, further free radical reactions are prevented.

Research[]

The U.S. National Institutes of Health report that BHA is reasonably anticipated to be a human carcinogen based on evidence of carcinogenicity in experimental animals. In particular, when administered in high doses as part of their diet, BHA causes papillomas and squamous cell carcinomas of the forestomach in rats and Syrian golden hamsters.[5] In mice, there is no carcinogenic effect;[5] in fact, there is evidence of a protective effect against the carcinogenicity of other chemicals.[4]

When examining human population statistics, the usual low intake levels of BHA show no significant association with an increased risk of cancer.[6] The state of California has, however, listed BHA as a carcinogen.[7]

The European Commission has conducted an evaluation of literature. They noted the lack of potential for the compound to induce carcinogenic effects in humans; studies showing carcinogenic effects in hamsters are not relevant to humans (which lack a forestomach). Also noted is that endocrine disruption, if any, is only likely to be present at levels vastly exceeding the intake as a food. [8]

See also[]

References[]

  1. ^ "BHA and BHT". Retrieved Nov 20, 2009.
  2. ^ "SciFinder — Experimental properties for 121-00-6". Retrieved Nov 20, 2009.
  3. ^ Hazardous Substances Database, National Library of Medicine
  4. ^ a b Lam, L. K.; R. P. Pai & L. W. Wattenberg (1979). "Synthesis and chemical carcinogen inhibitory activity of 2-tert-butyl-4-hydroxyanisole". J Med Chem. 22 (5): 569–71. doi:10.1021/jm00191a020. PMID 458807.
  5. ^ a b Butylated Hydroxyanisole (BHA), CAS No. 25013-16-5 Archived 2010-06-05 at the Wayback Machine, Report on Carcinogens, Eleventh Edition, National Institutes of Health
  6. ^ Botterweck AAM, Vergaen H, GoldBohm RA, KleinJans J, van den Brant PA (2007). "Intake of Butylated Hydroxyanisole and Butylated Hydroxytoluene and Stomach Cancer Risk: Results from Analyses in the Netherlands Cohort Study". Food and Chemical Toxicology. 38 (7): 599–605. doi:10.1016/S0278-6915(00)00042-9. PMID 10942321.
  7. ^ "Known Carcinogens and Reproductive Toxicants (California Proposition 65)". Scorecard. Archived from the original on 2019-08-14. Retrieved 2011-05-29.
  8. ^ "Scientific Opinion on the re-evaluation of butylated hydroxyanisole - BHA (E 320) as a food additive". EFSA Journal. 9 (10): 2392. 2011. doi:10.2903/j.efsa.2011.2392.
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